How To Ask A Girl Out On A Date In 10 Simple Steps

How To Ask A Girl Out On A Date In 10 Simple Steps


So you have found a woman you are interested in — or have been interested in for quite some time — and you think you are on your way to properly mustering up the courage to ask her out on a date. Congratulations! You are almost ready to take the first step to the rest of your life, or — at the very least — a very fun and amorous time with the lady who has quickened your pulse as of late. Asking a woman on a date can be exciting, but it can also provoke anxiety. Nervousness experienced around the woman of interest, along with the fear of rejection can be enough to make you forego asking for a date in favor of remaining steeped in the casual dating scene that has become so omnipresent in our culture.


Have no fear, because I have taken it upon myself (you’re welcome) to outline the various facets that play a role in asking a woman on a date, as well as the best ways to prepare, and some no-fail (or almost no-fail) techniques that will help you snag a date with the woman who could potentially be the Bonnie to your Clyde…or something like that. Let’s take a look at the 10 best ways to ask a woman on a date:

10Ask Her To Lunch

Ladies Love Lunch. Don’t be afraid to order something delicious and offer to share!

Guess who loves lunch?? If your answer to that question was “everybody” then congratulations. You are correct. Lunch dates can be a great suggestion for a first date, because they are 1) something every single person is (hopefully) going to be partaking in on a regular basis anyhow, so why not have a companion to accompany you on what The Toast’s fictional Dad Magazine calls “afternoon’s breakfast” 2) it’s less pressure both on you and your lady in question. First dates in general are meant to be more casual, as you are just starting to get to know the person, so a casual location and time is befitting of  a first date.


Moreover, you can sometimes secure a date more easily with a “let’s go to lunch” lead because it’s innocuous enough to barely even pass for a date. If your crush also happens to work in the same office as you, this makes the suggestion even more palatable. From there, you can get to know each other better and work your way up to something more intimate, like dinner plans.

9Ask Questions and Make Comments That Are NOT Based On Her Looks

Women have non-physical positive attributes?

As a woman, I’m certainly not against being complimented and (read: non-creepy) comments on my appearance can be very flattering in certain scenarios. However, when you are initially approaching a woman for a date, steer clear of comments that are centered on her appearance. Women are subjected to various lascivious remarks and unwanted attention at places like bars regularly. I’m both a freelance writer and a redhead. What was the point of me mentioning that? I’m glad you asked!

There are plenty of times I enjoy a glass of wine or a pint of quality lager by myself or with a girlfriend or two on my off hours. If I am by myself, I am often poring over my kindle or iPhone, reading works from authors that I garner inspiration from. I cannot even begin to list the amount of men that have come up to me with a leering grin and noted, “you have [insert subtle groan here] beautiful red hair” or “You are quite the beautiful lady,” OR “what’s a pretty woman like you doing all by yourself?” I am perfectly content being by myself for a brief nightcap and, yes, I am aware that I have a gingery coif (thanks for pointing that out with the aforementioned guttural groan), and no, comments on my appearance are not welcomed when there seems to be unspoken sentiments attached to them that make me feel unsafe.


If a man asks me questions about what I am reading on my kindle, if I am “from around here” or “what do you do for a living?” I am usually more than happy to oblige in giving an answer that doesn’t include a “GTFA from me” look. There are no words to properly articulate how refreshing it is for us single ladies to have a man take a genuine interest in our interests and career pursuits — pursuits that were not at our disposal decades ago. Ask the lady that is your current source of amore about her interests, work, and the like. Even if she looks beautiful, you can save the “wow, you look great!” Comments for the actual date once you secure one. Trust me on this one.

8Suggest A Fun Group Outing

This looks like a fun first date

Just as avoiding comments on a woman’s appearance when approaching her serves in being non-threatening and bettering your chances of securing a date, so try suggesting a group date rather than an intimate one-on-one rendezvous. This not only takes the pressure off, but it offers an opportunity to get to know the woman in a setting where you can also show off your personable skills by interacting with your — and her —friends. Expert Beacon offers some great tips on how to word your invitation if taking this approach.


According to Expert Beacon author, Dave Pounder,  “If she is a co-worker, perhaps you could say, ‘A bunch of us are heading over to the pub for happy hour after work, do you want to join us? Bring others from your department. It would be fun!’ If she is a neighbor, ‘Hey there, a bunch of the neighbors are thinking of having a pool party sometime in the next few weeks. Would you attend if we organized one? Know any other neighbors you could invite?’” He goes on to note the importance of gender neutrality in these invites, stating: “This gender-neutral, non-threatening approach is ideal for breaking the ice and putting you on her radar. Once at the event, follow the same gender-neutral line of questioning mentioned above. If, at the event, you find yourself in a solid conversation, suggest that you hang out sometime.”

7Exude Confidence

Summon your inner-Donald

Everett Collection /

If you’re not feeling confident, try adopting the old adage of “fake it until you make it.” I completely understand how anxiety-inducing asking someone for a date can be. However, if you allow your nerves and insecurities (of which we all have, so don’t feel bad) to overtake your psyche, then you fall into the trap of making a negative belief come true. The aforementioned is consequence of something known as a self-fulfilling prophecy (a term first coined by Robert Merton in 1948), which is when a fallacious idea one has of themselves or their future becomes true. Self-fulfilling prophecies can be your best friend or your worst enemy. When you believe something positive about yourself, others tend to agree based on the confidence you exude. Conversely, when you believe something to be false, you exude that self-deprecation as well, and others will fall in line with this exuded ideology.


I once dated a man who was kind, had a stable career, and made me laugh. I absolutely adored him, but unfortunately he was often crippled by his own unfounded insecurities. He would put me up on a pedestal, consistently waxing poetic and repeating the mantra, “I don’t know why a girl like you is going out with a guy like me.” Um, I was going out with you because I thought you freaking rocked and was attracted to you! Duh.


Women crave a relationship with a man who has confidence without being cocky. The adage “nice guys finish last” is flawed, in my humble opinion. Rather, the phrase may need to be updated to something like: “nice guys with zero self-esteem and unremitting self-deprecation” finish last. Although the wide-held belief is that women prefer jerks over nice guys, I can tell you for a fact that this simply isn’t so — at least not once you get past your late teens and early twenties. We want a man who can treat us well and pay compliments while also being sure of themselves; we want a man who can make time for us but also has a life of their own that is not centered on our every beck and call. To further illustrate this point, Comedy Central’s Inside Amy Schumer titled Hello M’Lady” that makes for a good reference point.


If you happen to find yourself with a woman who does seem to have “worship the ground I walk on and drain your bank account in order for me to deem you worthy of my attention” as a prerequisite to dating her — RUN. Run as fast and as far as you can from this woman! That isn’t the type of person you want to take out for a date or even converse with for more than 30 seconds.

6Avoid Too Many Libations

Wuuuutzz ur name again?

There’s nothing wrong with utilizing a cocktail or two beers to muster up some extra courage when you want to ask a woman out on a date. That being said, it doesn’t take too long for “liquid courage” to foray into “what is wrong with that guy?!” territory after a delayed effect from that last shot of whiskey rears its ugly head just as you were about to get a girl’s digits. I remember one point when I had visited my favorite watering hole for a night cap, a man sidled up to me at the bar and began a conversation. He wasn’t being lewd or overbearing. He told me he was new in town, and as he was also a freelancer, we had much to talk about in them space of fifteen minutes. I had been planning on leaving after one beer, but he had been charismatic enough to convince me to enjoy one more and continue our conversation.


Apparently he had been at the bar for a significantly longer time than I had — and had enjoyed quite a few more libations than I had — because it was seemingly out of nowhere that his entire demeanor changed. His speech became slurred, chortling laughter would emanate from his gut when I hadn’t even made a joke, and his eyes took on a reddened glazed-over look that told me I needed to scurry ASAP to a sign marked “Exit”.


In other words, take it slow. Even if some of your nervousness shines through, many women (me, included) can find some slight awkwardness more appealing than an overly debonaire casanova.

5Sidle Up, But Not Too Close

This might be a little too cloase

You obviously are going to want to get close to the person you’re thinking about asking out on a date — both figuratively and literally. However, you don’t want to become overbearing. According to the Social Issues Research Centre’s (SIRC) Guide to Flirting by Kate Fox, start a conversation with your potential date by positioning yourself approximately four feet away, to keep an interested yet non-threatening distance. “If you receive a positive response…move in to ‘arm’s length’ (about 2ft 6 in).”


Women are often inundated with overbearing advances and situations which conjure feelings of discomfort. It’s not that we don’t want to be approached — we just don’t want to be approached in the wrong way. With the aforementioned rule of thumb, you can ensure that the lady of interest feels safe and secure in conversing with you. As the conversation moves forward and she reciprocates your interest by: mimicking your body movements and gestures; meeting your gaze and holding it for more than a couple seconds, and smiling, you can move forward to more flirtatious — albeit, innocuous — gestures.


Fox goes on to note that “breaking the touch barrier” can be the next step in flirting once you have established that the conversation is going in a flirtatious direction, and that it’s ok to go beyond distance that is “arms length.”


“As a general rule, the arm is the safest place to touch an opposite-sex stranger. (Back pats are equally non-sexual, but are often perceived as patronising or overbearing.) A brief, light touch on the arm, to draw attention, express support or emphasise a point, is likely to be acceptable and to enhance your companion’s positive feelings towards you.”

4Make Sure This Is An Appropriate Person To Be Asking Out

Is she available? Are you?

Before taking the plunge into asking someone on a date, it is important to quell possible fears such as: does this person have a boyfriend? Is she married? Is she single, but emotionally attached to someone else? You don’t want to unwittingly overstep your boundaries, or — even worse — end up in the dreaded “friend zone.” If you and your potential date run in similar groups of friends, you can usually find out the person’s marital status or attachments from someone you trust who also happens to be “in the know.” Conversely, if you don’t know much about this person outside of a happenstance meeting, you can usually assess their marital status by weaving the subject casually into your conversation.


For example: “I haven’t been here in a while. My friend and her husband were the ones to introduce me to this place. Do you and your boyfriend come here often?” Questions like this offer an innocent — and flattering — assumption that the woman you are vetting as a potential date is attached. If she is attached, she can simply respond with a “yes” or a “no, my boyfriend/husband and I haven’t been here before.” Thus, you have learned that the woman is off-limits without having to subject yourself to any awkwardness by outwardly asking for a date. If the woman is unattached, she will likely beam “no, I don’t have a boyfriend,” and from there you can further ease into more romantic territory, and officially ask for a date.

3Utilize Your Inner Comedian

Channel the Rodney

Featureflash /

It may seem hackneyed to state that women love a man with a sense of humor, but — to be honest — behind every cliche is some truth. Women love to laugh (I mean, really, who doesn’t?) and the ability to deftly infuse some humor into conversation is something we all find attractive. Men tend to be more visual than women, which is why women can often be seen getting wooed by the funny guys rather than the agro dudes that resemble something that may have walked out of a photoshopping session (no hate, of course — I’m just trying to say that women have more variable tastes than some may realize).


In order to investigate some of the most successful ways to ask a woman on a date, AskMen scoured Reddit and posted several tales from women on ways they were adequately wooed (how’s that for alliteration?). One redditor offered a story on how one clever Casanova used their mutual interests to snag a date:


“ A guy I know who lives out of state had just became a doctor. We were joking on Facebook about something and he offered to write me a prescription for some antibiotic. He was very persistent about it and about getting my address for this purpose. A week later, I got a prescription for “one date” with him. It was adorable and possibly medical malpractice at the same time.”

2Embrace The Idea Of Rejection

Learn to Roll with the punches

There are few things that can garner as much fear and anxiety as the idea of rejection. Being rejected can lead to several things: embarrassment; self-deprecation, and insecurity. It is important to note, however, that the aforementioned consequences are not life-threatening, and any subsequent anxiety will subside. Moreover, even if you do get rejected, the fact that you took a chance and conquered fears can be empowering all on its own.


The Distilled Man’s Kyle Ingham suggests taking a “buddhist approach” to rejection, where any potential losses from said rejection are eradicated in favor of an outcome that can only lead to personal gains. Ingham states: “[Buddhists] have a phrase that goes something like ‘See the glass as already broken.’ They don’t overreact when something is destroyed or when a glass breaks because that glass is already broken…Asking a woman out should be the same. If she says no, it’s not like you’re really LOSING something. Instead of getting bent out of shape if she says no, just say to yourself, ‘ah well, her loss.’ One thing the Buddhists won’t tell you is that asking women out is a numbers game. The more you get out there, the more you increase your chances of a woman saying yes. Once you realize that it takes 9 no’s to get to a yes, the no’s don’t sting as much.”

1Just Do It

If you don’t ask her out, some other chump definitely will

Inevitably, the one thing that stands between you and asking a woman out is…well…you. The aforementioned items on this list offer various forms of preparation, flirtatious techniques, and other ways to ease the pressure in taking on one of the most anxiety-inducing facets of our current dating culture. I understand that rejection — albeit, the very idea of rejection — is a proverbial pill that is extremely difficult to swallow. What’s worse than rejection, though? One word: regret.


We don’t want to forego taking a risk and end up in mindset that is steeped in “could of,” “would of,” “should have’s.” Even if the woman catching your eye says “no,” to your romantic invitation, understand that this is not the end of the world, and that so-called “rejection” could be something that leads you one step closer to a woman that is actually perfect for you to offer a resounding “YES” to a date with you. Look at asking a woman out as a win-win, conjure the inner buddhist we mentioned previously and just freaking go for it, already! Then, I suggest you promptly email ListLand about your successes and/or respond in the comments section so that we all can provide you with some virtual accolades.


Good luck!